Claims
- 1. A racemic compound of the formula ##STR23## wherein A is --CH.sub.2 --CH.sub.2 --R.sub.7
- R.sub.1 is hydrogen or lower alkanoyl,
- R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,
- R.sub.5 is lower alkyl,
- R.sub.7 is a heteroaromatic radical selected from thienyl or pyridyl or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which heteroaromatic radical or aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl-lower alkoxy of 2-7 carbon atoms, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, amino, amino-lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy or pyridyl, or on adjacent carbons can be ##STR24## wherein R' is hydrogen, lower alkanoyl, trifluorocetyl and R" is hydrogen or lower alkyl,
- or an enantiomer thereof or a salt thereof.
- 2. A compound, in accordance with claim 1, wherein R.sub.1 is hydrogen, R.sub.2 -R.sub.5 are methyl and A is --CH.sub.2 --CH.sub.2 R.sub.7.
- 3. A compound according to claim 1 wherein the compound is rac-3,4-dihydro-2,5,7,8-tetramethyl-2-(2-phenylethyl)-2H-1-benzopyran-6-ol
- 4. A compound according to claim 1 wherein the compound is rac-3,4-dihydro-2,5,7,8-tetramethyl-2-[2-(2-thienyl)ethyl]-2H-1-benzopyran-6-ol.
- 5. A compound according to claim 1 wherein the compound is rac-4-[2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethyl]-1,2-benzenediol.
- 6. A compound according to claim 1 wherein the compound is rac-3,4-dihydro-2,5,7,8-tetramethyl-2-[2-(3-pyridinyl)ethyl]-2H-1-benzopyran-6-ol.
- 7. A compound according to claim 1 wherein the compound is rac-3,4-dihydro-2,5,7,8-tetramethyl-2-[2-(2-pyridinyl)ethyl]-2H-1-benzopyran-6-ol.
- 8. A compound according to claim 1 wherein the compound is rac-2-[(3-acetyloxy-4-methoxyphenyl)ethyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 9. A compound according to claim 1 wherein the compound is rac-3,4-dihydro-2,5,7,8-tetramethyl-2-{[4-(3-pyridinyl)-2-phenyl]ethyl}-2H-benzopyran-6-ol.
- 10. A compound according to claim 1 wherein the compound is rac-3,4-dihydro-2,5,7,8-tetramethyl-2-{[5-(2-pyridinyl)-2-thienyl]ethyl}-2H-1-benzopyran-6-ol.
- 11. A compound according to claim 1 wherein the compound is rac-4-[2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethyl]1,2-benzenediol-2-acetate.
- 12. A compound according to claim 1 wherein the compound is rac-{2-[5-(aminomethyl)-2-hydroxy-3-methoxyphenyl]ethyl}-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol hydrochloride.
- 13. A compound according to claim 1 wherein the compound is rac-3,4-dihydro-2-[2-(3-methoxyphenyl)ethyl]-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 14. A compound according to claim 1 wherein the compound is rac-2-[2-(5-butyl-2-thienyl)ethyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 15. A compound according to claim 1 wherein the compound is rac-5-[2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benopyran-2-yl)ethyl]-2-hydroxybenzoic acid methyl ester.
- 16. A pharmaceutical composition comprising an effective amount of a racemic compound of the formula ##STR25## wherein A is, --CH.sub.2 --CH.sub.2 --R.sub.7
- R.sub.1 is hydrogen or lower alkanoyl,
- R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,
- R.sub.5 is lower alkyl,
- R.sub.7 is a heteroaromatic radical selected from thienyl or pyridyl or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which heteroaromatic radical or aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl-lower alkoxy of 2-7 carbon atoms, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, amino, amino-lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy or pyridyl, or on adjacent carbons can be ##STR26## wherein R' is hydrogen, lower alkanoyl, trifluorocetyl and R" is hydrogen or lower alkyl,
- or an enantiomer thereof or a salt thereof, and an inert carrier.
- 17. A pharmaceutical composition, in accordance with claim 16, wherein R.sub.1 is hydrogen, R.sub.2 --R.sub.5 are methyl and A is --CH.sub.2 --CH.sub.2 R.sub.7.
- 18. A method of treating disease states caused or aggravated by excessive oxidative metabolism of arachidonic acid which comprises administering to a host requiring such treatment an effective amount of racemic compound of formula ##STR27## wherein A is, --CH.sub.2 --CH.sub.2 --R.sub.7
- R.sub.1 is hydrogen or lower alkanoyl,
- R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,
- R.sub.5 is lower alkyl,
- R.sub.7 is a heteroaromatic radical selected from thienyl or pyridyl or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which heteroarmatic radical or aromatic radical may optionally be substituted by one or more substitutents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl-lower alkoxy of 2-7 carbon atoms, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, amino, amino-lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy or pyridyl, or on adjacent carbons can be ##STR28## wherein R' is hydrogen, lower alkanoyl, trifluorocetyl and R" is hydrogen or lower alkyl,
- or an enantiomer thereof or a salt thereof, and an inert carrier.
- 19. A method in accordance with claim 18, wherein R.sub.1 is hydrogen, R.sub.2 --R.sub.5 are methyl and A is --CH.sub.2 --CH.sub.2 R.sub.7.
Parent Case Info
, now abandoned.
This is a division of application Ser. No. 07/627,523 filed Dec. 14, 1990 now U.S. Pat. No. 5,132,310, which is a Divisional of Ser. No. 07/367,082 filed Jun. 16, 1989, now U.S. Pat. No. 5,015,661, which is a continuation in part of Ser. No. 230,094, filed Aug. 9, 1988--Abandoned.
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61148173A |
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JPX |
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JPX |
61-267570A |
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WOX |
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Divisions (2)
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Number |
Date |
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Parent |
627523 |
Dec 1990 |
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Parent |
367082 |
Jun 1989 |
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Continuation in Parts (1)
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230094 |
Aug 1988 |
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